Imidazole → HCID 13065831, compound

HRID 1702464Notes

Reaction equation

HRID 1702464 reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>ClCCl>[N:10]1([CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 87885Chloromethyl pivalate

Product 1

HCID 13065831HCID 13065831, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.95 g (0.013 mole) of pivaloyloxymethyl chloride, dissolved in 20 ml of dichloromethane, were added 1.76 g (0.026 mole) of imidazole. The reaction mixture was refluxed for 32 hours, then was cooled and filtered. The filtrate was concentrated in vacuo to give an oil which was triturated with 100 mL of ether. The ether was decanted and concentrated in vacuo to give 1.30 g (55% yield) of the desired ester: IR (neat) 1720 cm-1 (s) (C=O); NMR (CDCl3) δ 7.7 (s, 1, N=CH--N), 7.07 (s, 2, N--CH=CH--N), 5.9 (s, 2, N--CH2 --O2C), and 1.17 (s, 9, (CH3)3C).

Workup

  1. temperatureThe reaction mixture was refluxed for 32 hours
  2. temperaturewas cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give an oil which
  6. customwas triturated with 100 mL of ether
  7. customThe ether was decanted
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f202f06eb0164d0dad32f17058aff691
Source dataset
uspto-grants-1983_04
Patent number
US04381307

Reaction notes

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